Women's History Month: The Small Business Advocate

I intentionally choose to work with a diverse mix of business owners across the metro Detroit region. Professionally, it’s to improve my skills and problem-solving experiences to better serve my clients, but personally, it’s because each client has such a unique story to tell depending on their deeply personal obstacles and experiences. Many of my clients are women and many experience challenges most male business owners never have to encounter and solve in order to move forward. Yet these women do on a daily basis in order to build their businesses, grow as people, and achieve their dreams. For Women’s History Month, I’m uplifting the many ladies I have the honor to support on their entrepreneurial journey.

Jennyfer Crawford - Ask Jennyfer


When did you have your first business idea? What helped you decide to launch? 

I feel like everyone with an entrepreneurial spirit had their first business idea when they were kids, even if it was just a lemonade stand. I was the same way. As an adult, the idea of helping others inspired me to launch Ask Jennyfer. I knew what I went through working my 9-to-5 and it wasn’t a good fit. I wanted to make it my mission to help others just like me who have a passion for doing something they love. 

What do you really love about your business? 

What I really love about Ask Jennyfer is that I get the opportunity to help others in some way every day. The small business owners I work with have amazing stories and those stories are what motivates me to create platforms to increase their exposure to potential clients and enhance the overall community of entrepreneurs.

What don't you like doing within your business? 

One thing I don't like doing within my business is saying “No.”

I want to be able to help everyone and also give everyone access to these opportunities, like my small business event All Things Detroit. But when we are sold out or fully-booked, I have to say no and I don't like that very much. 

What can you improve on with your business?

As a business owner it’s definitely important to recognize where you can enhance or improve. I am working on delegating more to others. I always feel like I can do it all but in the end it's all about having a great team on your side - and I am in the process of building that. 

What's one the biggest lessons you've learned since starting your business? 

One of the biggest lessons I learned is to trust your instincts and go what feels right to you. When you listen to outsiders sometimes that’s not always best. 

How does being a woman impact your business? How does being a black woman impact your business? What's something people should know about the experience of being a black woman/woman business owner? 

In my experience being a woman in business is really hard. You are dealing with different stereotypes. We are sometimes treated as emotional creatures. If you are a black woman in business,  it’s 10 times harder. In my experience when you are a black woman in business it is hard to being taken seriously. There can be fewer opportunities and you have to prove yourself regardless of where you are in your career. I deal with this every day and that is why I create opportunities - not only for me - but for other women just like me that are experiencing the same challenges. 

How do you balance your personal and professional life, and your mental well-being?

After being in business for 7 years I am just now figuring out ways to balance personal and professional life. I definitely am working on making time for myself while maintaining my business.  I feel that it is important to have an outlet not only as a business owner but as a human being, so I have a counselor that I speak with once a week and that helps me maintain my mental/emotional well-being.

What's one (or two) myths about entrepreneurship most people think is true?

There are so many myths about entrepreneurship and I think the number one myth is that entrepreneurs have a lot of money. Not so. And secondly there is a myth that entrepreneurship is easy. All false. What you put into entrepreneurship is what you get out of it and you have to work really hard before you see a lot of money, in most cases, 

What's one piece of bad advice you've received about your business?

One piece of bad advice I received about my business is that I need to book celebrity host for my events. I was told that is the only way I would get people to understand my vision. I did not take that advice and I have been able to grow my brand successfully without using those tactics.

Any super solid advice?

Super solid advice I received and the advice I live by is to always be innovative.

Whom do you seek advice from for your business? 

I seek advice from my team and also mentors who have been running their businesses for a long time and understand the challenges we face.

What do you have coming up on the horizon that you're excited about? 

Well, I just launched my new platform All Things Ticketing which is a ticket hub for small businesses. Coming this summer, I will have a new mobile app,  Meet me at the Markets curated by Ask Jennyfer, available to promote all of the new markets and events I will be curating this year. 

Where do you see your business in the next year? In the next five years? The next ten years? 

Within the next year I plan to curate more markets and expand in other states. It's something I really love to do and in the next 5 to 10 years plan to see Ask Jennyfer creating markets all over the world and developing more platforms to increase exposure for small businesses.

Anything else you want to share? 

Running a small business takes hard work, dedication and I wouldn't change anything about this journey. Speak what you want into existence, but you have to be prepared for the journey.